Virginia has no shortage of places worth visiting — colonial history in Williamsburg, mountain scenery along the Blue Ridge, wineries in every direction. But ask seasoned Virginia travelers where they keep going back to, and a surprising number of them will say Staunton.
Small, walkable, and genuinely authentic, Staunton sits in the Shenandoah Valley at the crossroads of Virginia history, outdoor access, and a cultural scene that punches well above its size. Here is why it deserves a spot on your 2026 travel list.
A City With Real History
Staunton was established in 1747 and served as the Confederate capital of Virginia for a brief period during the Civil War. It is the birthplace of Woodrow Wilson — the 28th President of the United States — and his Presidential Library and Museum remains one of the most thoughtfully curated presidential libraries in the country.
The architecture alone is worth the trip. Staunton's downtown historic district is one of the best-preserved Victorian commercial districts in Virginia, with five National Register Historic Districts within the city limits. Walking Beverley Street feels less like a heritage tourism exercise and more like the city just never got around to tearing anything down — which, here, is entirely a compliment.
The Arts Scene Nobody Talks About
Staunton is home to the American Shakespeare Center and its Blackfriars Playhouse — the only operating recreation of Shakespeare's original indoor theater in the world. The theater draws art lovers from across the Mid-Atlantic, and performances sell out regularly.
Beyond Shakespeare, the city supports a strong independent arts community — galleries, live music venues, and a creative culture that has quietly made Staunton one of Virginia's most interesting small cities.
Outdoor Access That Surprises People
Staunton sits on Interstate 81 roughly 25 minutes from the entrance to Shenandoah National Park and the northern end of the Skyline Drive. The Blue Ridge Parkway is equally accessible. For hikers, cyclists, and anyone who wants to spend a morning on a trail before lunch back in town, the location is nearly perfect.
Outdoor options within easy reach:
- Shenandoah National Park — 25 minutes east
- Skyline Drive — scenic driving route along the Blue Ridge crest
- Ramsey's Draft Wilderness — old-growth forest and stream hiking
- Chimney Hollow and Elliott Knob — local trails with valley views
Where and What to Eat
Beverley Street is Staunton's main dining corridor and it overdelivers for a city this size. Expect serious farm-to-table cooking, craft beer, and independent restaurants that have been here long enough to know what they're doing. Saturday mornings bring the Staunton Farmers Market, worth building an itinerary around.
The Shenandoah Valley wine trail runs through the broader region, making Staunton a natural base for a wine-focused weekend as well.
When to Visit
Staunton rewards every season, but summer and fall are peak:
- June–August: Shakespeare season in full swing, warm evenings, Shenandoah at its greenest
- September–October: Fall foliage on the Blue Ridge, cooler hiking weather, harvest dining
- December–February: Holiday events, quieter streets, lower rates
- March–May: Wildflowers in Shenandoah, wine trail traffic, spring programming at Blackfriars
Where to Stay
Hotel 24 South is the only historic hotel in downtown Staunton — a 1924 Colonial Revival building steps from Blackfriars Playhouse, the Woodrow Wilson Library, and everything on Beverley Street. Rooms are cozy, the building has genuine character, and the staff know Staunton well enough to give recommendations that aren't just a list of the most-reviewed places on the internet.
If Staunton is Virginia's best kept secret, Hotel 24 South is where you stay when you're finally in on it. View packages and book at hotel24south.com/specials.